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Compound Detail

CHEMBL637

VENLAFAXINE
💊 Approved Drug
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💊 Approved Drug
COc1ccc(C(CN(C)C)C2(O)CCCCC2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL637
Name VENLAFAXINE
Phase Approved
Structure Type MOL
InChI Key PNVNVHUZROJLTJ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Alventa xl Amphero xl Bonilux xl Depefex xl Efectin Efexor Efexor xl Foraven xl Kanghong Mentaven xl NSC-758676 Politid xl +18 more
9
Targets
56
Activities
3
Assay Types
15
PK Parameters
20
Publications
30
Known Names
2
Indications

Molecular Properties

277.4
MW (Da)
3.04
ALogP
3
HBA
1
HBD
32.7
PSA (Ų)
0.90
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1993
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -faxine
USAN Year 1989

Extended Properties

Molecular Formula C17H27NO2
MW 277.41
Aromatic Rings 1
Heavy Atoms 20
NP-Likeness 0.13

Indications

Depressive Disorder Depressive Disorder

ATC Classification

N06AX16
venlafaxine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Drug Warnings

Black Box Warning
psychiatric toxicity
Country: United States

Activity Summary

IC50 35 meas. best 8.14
Ki 16 meas. best 8.42
Kd 5 meas. best 8.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 8.42 7.685 3.8 4
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 8.14 7.5013 7.2 8
Sodium-dependent serotonin transporter
CHEMBL228
 Kd 8.05 8.05 8.9 1
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 7.6 7.4367 25.0 3
Alpha-1A adrenergic receptor
CHEMBL319
 IC50 7.05 6.9533 90.0 3
Sodium-dependent serotonin transporter
CHEMBL313
 IC50 7.0 6.708 100.0 5
Norepinephrine transporter
CHEMBL304
 Ki 6.86 6.5 138.0 2
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 6.83 6.0578 149.0 9
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 6.68 6.115 210.0 4
Sodium-dependent dopamine transporter
CHEMBL338
 Ki 6.44 6.44 360.0 1
Transporter
CHEMBL6184
 IC50 6.19 6.02 640.0 2
Norepinephrine transporter
CHEMBL304
 IC50 6.19 5.9367 640.0 3
Sodium-dependent noradrenaline transporter
CHEMBL222
 Kd 5.97 5.97 1060.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 5.44 5.36 3620.0 2
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 5.35 5.134 4430.0 5
Sodium-dependent dopamine transporter
CHEMBL238
 Kd 5.03 5.03 9300.0 1
ADMET
CHEMBL612558
 Kd 4.42 4.42 38200.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 59.0 mL.min-1.g-1 Homo sapiens
CL 14.0 mL.min-1.kg-1 Homo sapiens
CL 13.4 mL.min-1.kg-1 Homo sapiens
CL 14.0 mL.min-1.kg-1 Homo sapiens
CL 14.0 mL.min-1.kg-1 Homo sapiens
F 20.0 % Homo sapiens
Fu 0.73 - Homo sapiens
Fu 0.73 - Homo sapiens
Fu 0.73 - Homo sapiens
Fu 0.21 - Rattus norvegicus
Fu 0.123 - Sus scrofa
Fu 0.2419 - Rattus norvegicus
MRT 5.2 hr Homo sapiens
T1/2 5.0 hr Homo sapiens
T1/2 5.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent serotonin transporter Ki = 3.814 nM 8.42 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Sodium-dependent serotonin transporter IC50 = 7.18 nM 8.14 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Sodium-dependent serotonin transporter Kd = 8.9 nM 8.05 Equilibrium dissociation constant (KD) for Competitive binding between [3H]- imi... 9871604
Sodium-dependent serotonin transporter Ki = 11.0 nM 7.96 Displacement of [3H]citalopram from human SERT transfected in HEK293 cells after... 24900709
Sodium-dependent serotonin transporter IC50 = 20.0 nM 7.7 Inhibition of SERT 21413808
Sodium-dependent serotonin transporter IC50 = 20.0 nM 7.7 Inhibition of human SERT expressed in HEK293 cells assessed as decrease in [3H]-... 29039662
Sodium-dependent serotonin transporter Ki = 25.0 nM 7.6 Displacement of [3H]-citalopram from Sprague-Dawley rat brain SERT after 1 hr 24900709
Sodium-dependent serotonin transporter IC50 = 27.0 nM 7.57 Inhibition of human SERT expressed in human JAR cells 20378347
Sodium-dependent serotonin transporter IC50 = 31.0 nM 7.51 Inhibition of 5HT uptake at human SERT expressed in human JAR cells 18557608
Sodium-dependent serotonin transporter IC50 = 35.0 nM 7.46 Inhibition of serotonin reuptake at human SERT expressed in HEK293 cells 20724153
Sodium-dependent serotonin transporter IC50 = 36.1 nM 7.44 Inhibition of serotonin reuptake at human SERT expressed in HEK293 cells after 1... 24974340
Sodium-dependent serotonin transporter Ki = 37.0 nM 7.43 Inhibition of [3H]5-HT reuptake into rat frontal cortex synaptosomes 9871604
Sodium-dependent serotonin transporter Ki = 39.0 nM 7.41 Binding affinity to human SERT expressed in HEK293 cells after 60 mins in presen... 28731336
Sodium-dependent serotonin transporter Ki = 52.0 nM 7.28 Binding affinity to the serotonin transporter (SERT) measured by displacement of... 14640559
Alpha-1A adrenergic receptor IC50 = 90.0 nM 7.05 Inhibition of binding of [3H]imipramine to imipramine receptor in rat brain 1976813
Sodium-dependent serotonin transporter IC50 = 100.0 nM 7.0 Inhibition of uptake of tritiated serotonin (5-HT) into rat brain synaptosomes 1976813
Alpha-1A adrenergic receptor IC50 = 109.0 nM 6.96 Inhibition of binding of [3H]imipramine to imipramine receptor in rat brain 1976813
Sodium-dependent serotonin transporter Ki = 113.0 nM 6.95 Inhibition of [3H]5-HT uptake at human SERT expressed in HEK293 cells preincubat... 23602445
Norepinephrine transporter Ki = 138.0 nM 6.86 Inhibition of [3H]- NE reuptake into rat hippocampal synaptosomes 9871604
Alpha-1A adrenergic receptor IC50 = 140.0 nM 6.85 Inhibition of binding of [3H]imipramine to imipramine receptor in rat brain 1976813

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 436
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 73
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20724153 10.1016/j.bmcl.2010.07.021 Mus musculus 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
1976813 10.1021/jm00172a035 Rattus norvegicus 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
24900709 10.1021/ml400049p Unchecked 4
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
24974340 10.1016/j.bmcl.2014.06.026 Sodium-dependent dopamine transporter 4
24974340 10.1016/j.bmcl.2014.06.026 Sodium-dependent serotonin transporter 4
18426954 10.1124/dmd.108.020479 ADMET 4
24974340 10.1016/j.bmcl.2014.06.026 Sodium-dependent noradrenaline transporter 4
16019946 10.1080/00498250400028197 ADMET 4
19256501 10.1021/jm801441s No relevant target 3
21413808 10.1021/jm1013693 No relevant target 3
24900709 10.1021/ml400049p Sodium-dependent serotonin transporter 3

Data from ChEMBL 36 via Core Engine